tert-Butanol → tert-Butyl naphthalen-2-ylcarbamate

HRID 521597Notes

Reaction equation

HRID 521597 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1C(O)=O.CC[N:16]([CH2:19]C)CC.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.[C:38]([OH:42])([CH3:41])([CH3:40])[CH3:39]>C1(C)C=CC=CC=1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[NH:16][C:19](=[O:28])[O:42][C:38]([CH3:41])([CH3:40])[CH3:39]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 71232-Naphthoic acidHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 17231973tert-Butyl naphthalen-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Naphthoic acid (S13-1; 2.5 g, 14.3 mmol) in tert-BuOH (85 mL) and toluene (85 mL) was treated with Et3N (2.3 mL, 16.4 mmol), 3 Å molecular sieves (16.7 g) and diphenyl phosphorylazide (3.5 mL, 16.4 mmol). The reaction mixture was refluxed for 24 h. After cooling to rt, solid was filtered off through Celite and the solvent was removed under reduced pressure. The residue was dissolved in EtOAc (75 mL) and washed with 1N aqueous HCl (2×50 mL), saturated aqueous NaHCO3 (2×50 mL), dried over sodium sulfate and concentrated under reduced pressure. Chromatography (10% EtOAc in hexanes) afforded 2.5 g (71%) of S13-2. 1H NMR (500 MHz, CDCl3) δ 7.99 (s, 1H), 7.72-7.78 (m, 3H), 7.44 (t, J=7.8 Hz, 1H), 7.31-7.38 (m, 2H), 6.61 (br s, 1H), 1.55 (s, 9H); MS (ESI) m/z 244.02 [M+H]+.

Workup

  1. temperatureThe reaction mixture was refluxed for 24 h
  2. filtrationsolid was filtered off through Celite
  3. customthe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in EtOAc (75 mL)
  5. washwashed with 1N aqueous HCl (2×50 mL), saturated aqueous NaHCO3 (2×50 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customChromatography (10% EtOAc in hexanes) afforded 2.5 g (71%) of S13-2

Sources & evidence

ORD record
ord-7553088c0ede469093857ad4c9d786d0
Source dataset
uspto-grants-2016_05
Patent number
US09328114B2

Reaction notes

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